Tom Dwan Lost $50,000 Betting on Chess

May 10, 2023
Mark Patrickson

The world of poker throws up some interesting prop bets every now and then, but a $50,000 bet between Tom Dwan, David Benefield, and Greg Shahade 15 years ago is one that shows some players will never back down from an offered wager.

Tom Dwan Bets $50,000 He Can Beat an International Master

The story takes place in June of 2007, during the World Series of Poker, when two young poker players, David Benefield and Tom Dwan, were having a meal together. David mentioned that he had been playing chess with another poker player, Greg Shahade, who is an International Master and ranked among the top 100 players in the US. David was convinced that even if Greg gave up his queen, the most powerful piece on the board, he couldn't be beaten.

Tom, on the other hand, disagreed. He felt that with a queen up, he could trade off all the pieces on the board and use his extra queen to force a win. He even thought he could beat Greg with just a few pawns.

So, a bet was proposed, with Greg playing without a rook. If Tom could beat him, David would pay him $50,000. Tom, never one to back down from a good prop bet, agreed.

Greg Shahade, along with his father Mike and sister Jennifer, are well-known in the world of games. They grew up playing chess and eventually found their way to poker. Many chess players transitioned to poker during the poker boom of the mid-2000s, including FIDE Master Ylon Schwartz, who finished fourth in the 2009 WSOP Main Event, and Russian Grandmaster Alexander Grischuk, who considers poker to be his "second profession."

According to Jen, chess players naturally excel at poker because of their ability to devote themselves to rigorous study, practice, and pattern recognition. They know how to structure their study and understand how to analyze their weaknesses and strengths. This knowledge translates well to poker, where preparation and study are key to success.

“As soon as the advent of solvers came up, you started to study poker a lot more like you would study chess, and use the computer to analyze what you should do with each hand and try to remember the patterns,” Jen Shahade says. “I feel like it helped me in my understanding of the game and I was able to latch onto them very quickly. But it was also bad, because it meant that you just didn’t have time to study both games.”

David and Greg knew each other from the 2+2 poker forum and had mainly played online until this point. David reached out to Greg and asked how he would fare against a beginner if he started without a rook. Greg replied that he'd win virtually 100% of the time, which was music to David's ears. He invited Greg over to the house he shared with Tom and several other poker players.

The agreement was that Greg would play for a 10% freeroll, plus $2,000 if Tom backed out for any reason. Greg hemmed and hawed about changing his flight to make the game work, but he was secretly overjoyed. In 2007, $50,000 was a considerable amount for a prop bet. For chess players, that kind of money was unheard of outside of the top level.

The game itself was a nail-biter, with Tom Dwan sweating bullets as Greg steadily took his pieces. In the end, Greg won the game, and Tom was out $50,000.

David said: “I think he thought it would be a bit easier, but he didn’t seem too bothered by it either way. He’s always been pretty good at taking losses and this spot was no different.”

Tom asked Greg if he thought he had a 5% chance of winning. Greg said: “I didn’t know what to say. I worked so hard during the games that I felt some sense of danger. Whenever you work hard during a chess game you need to worry a little bit. However, looking back, it’s hard to imagine him actually winning. He simply has to survive so many pitfalls and then after all of that he has to demonstrate the technique to beat me from a winning position.”

Despite the loss, the bet created a lasting bond between the players, and the parallels between chess and poker have continued to grow over the years. Both games require strategy, mental toughness, and an ability to analyze patterns and make quick decisions.

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